Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
  • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
  • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
  • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
  • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
  • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
  • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
  • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
  • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
  • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
  • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
  • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S424/00—Drug, bio-affecting and body treating compositions
  • Y10S424/08—Systemic pesticides

Definitions

• X oxygen or sulphur
• R is hydrogen, alkyl or alkenyl
• R is alkyl or cycloalkyl
• R and R are each lower alkyl or alkenyl
• R is lower alkyl and R is alkoxyalkyl or haloalkyl
• R and R together with the nitrogen atom to which they are attached, form a heterocyclic ring and possess insecticidal and acaridicidal activity.
• a preferred group of compounds is one in which (a) R is methyl and R is lower alkyl or lower alkenyl, (b) R and R are both ethyl, propyl or allyl, or (c) R and R together with the nitrogen atom to which they are attached, form a heterocyclic ring, optionally containing 1 to 4 lower alkyl substituents attached to carbon atoms of the heterocyclic ring, selected from morpholino, thiamorpholino, l-pyrrolidinyl and l-piperidino.
• Preferred compounds are often those in which X in the above general formula is oxygen.
• R may have a straight or branched chain and may contain, for example, up to carbon atoms.
• R may be, for example, hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec.butyl, tert.butyl, n-pentyl, isopentyl, n-heyl, n-heptyl, l,ldiethylpropyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, allyl, l-propenyl 3-butenyl.
• R is hydrogen, or lower alkyl such as propyl, isopropyl, n-butyl, sec.butyl, isobutyl, tert.butyl and especially methyl-and ethyl.
• the radical R is alkyl or cycloalkyl and may contain, for example, up to 10 carbon atoms.
• R whenR is alkyl it may have a straight or branched chain, may be a primary, secondary or tertiary radical, for example, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec.- butyl, tert.butyl, l-methylbutyl, l-ethylpropyl, npentyl, isopentyl, isopentyl, tert.
• R when it is an alkyl group, are tert.butyl, sec.butyl, propyl, l-ethyl propyl, isopropyl and tert.pentyl.
• R When R is cycloalkyl it may contain, for example, up to 8, and more preferably from 3 to 7, carbon atoms in the cyclo ring.
• the cycloalkyl group may optionally contain one or more substituents on the ring, for example, one or more lower alkyl (especially methyl) substituents.
• a lower alkyl substituent is preferably inthe l-position, that is, it is attached to the cycloalkyl carbon atom joined to the imidazole ring.
• a further preferred group contains a lower alkyl (especially methyl) substituent in the l-position and in addition one or more loweralkyl (especially methyl) substituents in other positions on the ring. When there is more than one substituent on the cycloalkyl group they may be the same or different.
• R is cyclopropyl, l-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, cyclobutyl, l-methylcyclobutyl, cyclopentyl, l-methylcyclopentyl, l-ethylcyclopentyl, 2, 3 or 4 methylcyclopentyl, cyclohexyl, l-methylcyclohexyl, lmethylcyclohexyl containing 1, 2 or 3 further methyl substituents such as for example l,3-dimethylcyclohexyl, 1,4-dimethylcyclohexyl, l,3,3-trimethylcyclohexyl; l-ethylcyclohexyl, 2, 3 or 4 methylcyclohexyl, 2,4-dimethylcyclohexyl, 2, 3 or 4 ethylcyclohexyl, cycloheptyl
• R when R is cycloalkyl, it contains five or six carbon atoms in the cyclo ring and is cyclopentyl optionally containing one or more methyl substituents or cyclohexyl optionally containing one or more methyl substituents.
• Specific examples include cyclopentyl, l-methylcyclopentyl, cyclohexyl, l-methylcyclohexyl, l,3-dimethylcyclohexyl l,3,3-trimethylcyclohexyl.
• R and R may have a straight or brached chain and (a) R and R are the same or different and are lower alkyl or lower alkenyl; examples of lower alkyl are methyl, ethyl, propyl, isopropyl, or n-butyl, isobutyl, sec.butyl, tert.
• R is lower alkyl and R is alkoxyalkyl, containing for example from 3 to 6 carbon atoms such as ethoxyethyl, or lower haloalkyl containing for example from 1 to 6 carbon atoms and substituted by one or more halogen atoms preferably fluorine, chlorine or bromine. It is preferred that either (a) R is methyl and R is lower alkyl or (b) R and R are both ethyl or propyl.
• a specially preferred group of compounds is that in which R is methyl and R is lower alkyl, preferably containing 1 -4 carbon atoms and especially methyl.
• the group NRR when the group NRR is a heterocyclic group, it may contain 1 4 lower alkyl (especially methyl) substituents attached to carbon atoms of the heterocyclic ring.
• alkyl-substituted heterocyclic groups include, for example, 2,6- dimethylmorpholino, 4-methyl-l-piperidino, 2-methyll-piperidino, 2,6-dimethyl-l-piperidino and 2-ethyl-lpiperidino.
• NRR is heterocyclic it is preferably morpholino, l-pyrrolidinyl or l-piperidino.
• the compounds of the present invention have pesticidal activity and, for example, can be used to combat insects.
• the compounds have activity against Diptera such as the larvae of the sheep blow fly, Lucilia sericata and species of Hemiptera. For example they are of use against California red scale, Acridiella aurantii, the Comstock mealybug, Pseudococcus comsmcki and plant hoppers such as, for example, the green rice leafhopper, Nephorettix cincriceps.
• aphids such as Aphis fabae, Megoum viciae, Myzus persicae, Plwrudon humuli, Eriosoma langerum, Brevicoryne brassicae and Acryrhosiphon pisum.
• the compounds also have acaricidal activity against adults of the two-spotted mite, Tetranychus urticae and the citrus red mite, Panonychus citri.
• compositions which comprise as an active ingredient a compound of the present invention together with a diluent or carrier.
• the diluent or carrier may be a solid or a liquid, optionally in association with a surface-active agent, for example, a dispersing agent, emulsifying agent or wetting agent.
• compositions of the present invention may take any of the forms known in the art for the formulation of pesticidal or insecticidal compounds, for example solutions, aqueous dispersions, aqueous emulsions, dusting powders, dispersible powders, fumigants, emulsifiable concentrates and granules.
• Such compositions include not only compositions in a suitable form for application but also concentrated primary compositions which require dilution with a suitable quantity of water or other diluent before application. Dispersible powders and emulsifiable concentrates are typical examples of such primary compositions.
• the compositions comprise essentially a compound of the invention dispersed in an aqueous medium.
• a primary composition which may be diluted with water to form a dispersion having the desired concentration; the primary composition may be in any one of the following forms. It may be provided as a dispersible solution which comprises a compound of the invention dissolved in a water-miscible solvent with the addition of a dispersing agent. Alternatively it may be provided as a dispersible powder which comprises a compound of the invention and a dispersing agent.
• a further alternative comprises a compound of the invention in the form of a finely ground powder in association with a dispersing agent and intimately mixed with water to give a paste or cream. This paste or cream may if desired be added to an emulsion of oil in water to give a dispersion of active ingredient in an aqueous oil emulsion.
• Emulsions comprise essentially a compound of the invention dissolved in a water-immiscible solvent which is formed into an emulsion with water in the presence of an emulsifying agent.
• An emulsion of the desired concentration may be formed from a primary composition of the following types.
• a concentrated stock emulsion may be supplied comprising a compound of the invention in combination with an emulsifying agent, water and a water-immiscible solvent.
• an emulsifiable concentrate comprising a solution of a compound of the invention in a water-immiscible solvent containing an emulsifying agent.
• a dusting powder comprises a compound of the invention intimately mixed and ground with a solid pulverulent diluent, for example kaolin.
• a granular solid may comprise a compound of the invention associated with similar diluents to those which may be employed in dusting powders, but the mixture is granulated by known methods. Alternatively they may comprise the active ingredient absorbed or adsorbed on a pre-formed granular diluent for example fullers earth, attapulgite and limestone grit.
• the concentration of the active ingredient in the primary compositions of the present invention may vary widely and may be, for example, 5 w/w of the composition.
• the concentration'of the active ingredient in the compositions of the present invention for application to control pests, especially insects such as aphids, is generally within the range 0.001 10% w/w, especially 0.005 5% w/w.
• a method for combating pests, especially insects which comprises applying a compound of the present invention to the locus of the pests, i.e. the pests or their habitat.
• a particular embodiment of this feature is a method for protecting plants from insects, and in particular aphids, which comprises applying a compound of the present invention to the locus of the plants, i.e. the plants or their habitat.
• the active compound in combating pests the active compound can be applied on its own or preferably as one of the compositions described above. Direct treatment is often the preferred method, by for example, spraying, dusting or fumigation of plants infested with insects.
• the active compound can be applied to the soil in which plants are grown as granules or as a root drench. In such instances the active compound is absorbed by the roots of the plant and confers protection from the insects.
• a suitable application rate of the compound of the present invention is generally within the range 0.005 l0 lb./acre, more usually 0.01 5 lb./acre.
• the compounds of the present invention may be used to protect a variety of plants from aphids, for example ornamental plants such as roses, and crop plants such as fruit trees, leguminous crops. potatoes, hops, sugar beet, cotton, maize, rice and tobacco.
• a composition of the invention may comprise as active ingredient more than one compound of the general formula I and it may also comprise one or more additional pesticide or, for example, a fungicide or insecticide for example an organochlorine or organophosphorus insecticide.
• the compounds of the present invention may be prepared by a process which comprises reacting an imidazole of the general formula in which R and R are as hereinbefore defined with a carbamoyl halide or thiocarbamoyl halide of the general formula Z--CXNRR (Ill) in-which R, R and X are as hereinbefore defined and Z is halogen, for example, chlorine or bromine preferably chlorine.
• the reaction is suitably effected in the presence of an ineert organic liquid as the reaction medium, which is preferably a solvent for the reactants.
• the reaction is effected in the presence of a suitable acidbinding agent, for example a tertiary amine such as triethylamine or pyridine, in order to absorb the hydrogen halide produced in the reaction.
• a suitable acidbinding agent for example a tertiary amine such as triethylamine or pyridine
• the reactants are preferably reacted together at a temperature of from 0 to C.. for example from 50 to 95C.
• R .QEIfL R in which R, R and Z are as hereinbefore defined, Z being halogen preferably chlorine, with a secondary amine of the general formula HNR'R R and R being defined hereinbefore.
• the reaction is suitably effected in the presence of an inert organic liquid as the reaction medium, which is preferably a solvent for the reactants, at a temperature from 5 to 50C.
• a suitable acidbinding agent for example a tertiary amine such as triethylamine or pyridine.
• the compounds of the general formula IV are preferably prepared in situ from the imidazoles of general formula II by reaction with a carbonyl halide or thiocarbonylhalide CXZ in which Z is preferably chlorine, suitably in the presence of solvent and acid-binding agent; the secondary amine reactant then being added to the reaction product.
• the compounds of the present invention may also be prepared by a process which comprises reacting a carbonylbisimidazole or thiocarbonylbisimidazole of the general formula .il l
• reaction is suitably effected in the presence of an inert organic liquid as the reaction medium, which is preferably a solvent for the reactants. at a temperature of, for example, from 5 to 50C.
• the compounds of the general formula V are preferably prepared in situ by reacting an imidazole of the general formula ll with about 0.5 molecular proportions of a carbonyl halide or thiocarbonyl halide CXZ in which Z is preferably chlorine; the secondary amine then being added to this reaction product.
• the reaction is preferably effected in the presence of a suitable acidbinding agent, for example a tertiary amine such as triethylamine or pyridine.
• the reactions described above may give either or both of two isomeric products, depending on which nitrogen atom in the imidazole ring is substituted (the free hydrogen of the imidazole molecule of formula II can be associated with either of the ring nitrogen atoms). Since it may not be possible to distinguish between these isomers, the products of the present invention may be conveniently designated as l-(N,N-disubstituted-carbamoyl or thiocarbamoyl)-2-R -4(5)-R -imidazoles. This designation corresponds to formula I which encompasses both of the isomeric forms.
• EXAMPLE 2 In an analogous manner to that described in Example 1, there was prepared l-dimethylcarbamoyl-4(5)- methylimidazole, m.p. 58 60C. (crystallized from light petroleum b.p. C. and recrystallized from methylcyclohexane). The current state of our knowledge indicates that this compound is 1- dimethylcarbamoyl-4-methylimidazole.
• EXAMPLE 4 A mixture of 5.52 g. 4-tert.butylimidazole, 6.1 g. triethylamine, 8.95 g. morpholinocarbonyl chloride and 30 ml. dry tetrahydrofuran was boiled under reflux for 5 hours. The reaction mixture was diluted with 100 m1. methylene dichloride, cooled to room temperature, and washed with water to remove triethylamine hydrochloride. The resulting organic solution was dried over anhydrous magnesium sulphate and then evaporated to dryness. The resulting solid residue was recrystallized from ethanol to give 1-morpholinocarbonyl-4(5)- tert.butylimidazole, m.p. 129 130C. The current state of our knowledge indicates that this compound is l-morpholinocarbonyl-4-tert.butylimidazole.
• EXAMPLE 5 A mixture of 5.0 g. 4-tert.butylimidazole, 4.4 g. triethylamine, 5.9 g. l-piperidinocarbonyl chloride and 30 ml. dry tetrahydrofuran was boiled under reflux for 5.5 hours. The reaction mixture was cooled, filtered to remove triethylamine hydrochloride, and evaporated to dryness. The resulting solid residue was recrystallized from petroleum (b.p. 62 68C.) to give 1- piperidinocarbonyl-4(5 )-tert.buty1imidazole, m.p. 104 105C.
• the 4-tert.pentylimidazole used in the above reaction was prepared in the following way:
• the imidazole used in the above reaction was prepared in the following way.
• Bromopinacolone was added to a solution'of 72 g. potassium acetate in 700 ml. methanol and the resulting mixture was refluxed on a steam bath for 2 hours. It was then cooled, filtered and the filtrate added 60 with stirring to a solution of g. cupric acetate monohydrate in 800 ml. water and 1000 ml. 25 percent ammonia. A solution of 26 g. acetaldehyde in 200 ml. water was then added to the mixture which was heated on a steam bath for 5 hours with constant stirring.
• EXAMPLE 9 This example describes an alternative method of preparing l-dimethylcarbamoyl-4(5)-tert.butylimidazole.
• EXAMPLE 10 This example describes an alternative method of preparing l-dimethylcarbamoyl-4(5 )-tert.butylimidazole.
• the 4-(1-methylcyclohexyl)imidazole used in the above reaction was prepared in the following way.
• EXAMPLE 14 A mixture of 20.1 g. 4-(1,3-dimethy1cyclohexyl- )imidazole, ml. dry tetrahydrofuran, 28 ml. triethylamine and 16.2 g. dimethylcarbamoyl chloride were refluxed on a steam bath for an hour and then cooled. Methylene chloride was added and the solution washed with water, the first washing being re-extracted with methylene chloride. The methylene chloride extracts were dried over magnesium sulphate solution.
• the 4-( 1,3-dimethylcyclohexyl) imidazole used in the above reaction was prepared in the following way.
• the 2-methyl-4(5)-( l-methylcyclopentyl) imidazole used in the above reaction was prepared in the following way.
• the cuprous salt of the imidazole was collected, washed with water and suspended in 270 ml. of 4N acetic acid. While stirring, a solution of 34 g. potassium ferricyanide in 100 ml. water was added, and the precipitated copper complex removed and washed well with water. The combined supernatant liquors were basified to pH 9 10 with 5N sodium hydroxide and extracted several times with ether. The ethereal extracts were combined, washed with water and dried over anhydrous sodium sulphate. After evaporation of the solvent, the residue was crystallized from acetone to give the novel imidazole 2-methyl-4(5 l-methylcyclopentyl)imidazole, mp. 108C.
• the imidazole reactant was prepared in the following way.
• EXAMPLE 17 An emulsifiable concentrate suitable for dilution with water to form an aqueous emulsion was prepared from the following ingredients:
• Emulsifiable concentrates suitable for dilution with water to form an aqueous emulsion were prepared from the following ingredients:
• Nonlyphenoxypolyethoxyethanol 2.5 Xylene to 100.0% vol
• Emulsifiable concentrates containing the following compounds were prepared.
• butylimidazole EXAMPLE l9 Granules containing 5% w/w of the imidazole compound of Example 1 were prepared by impregnating granules of fullers earth (mesh size 20/40 British Standard Sieve) with a solution of the imidazole compound in xylene and then evaporating the xylene from the impregnated granules.
• EXAMPLE 20 Granules containing 5% w/w of the dimethylcarbamoyl-4( 5 l-methylcyclohexyl- )imidazole were prepared by impregnating granules of fullers earth (mesh size 20/40 British Standard Sieve) with a solution of the imidazole compound in xylene and then evaporating the xylene from the impregnated granules.
• EXAMPLE 21 An emulsifiable concentrate suitable for dilution with water to form an aqueous emulsion was prepared from the following ingredients:
• EXAMPLE 22 A dispersible powder was prepared from the following ingredients:
• Dyapol PT is an anionic dispersant based on the sodium salt of a sulphonated condensation product of urea/formaldehyde and cresol.
• EXAMPLE 23 Broad bean plants 3 5 cm. high were infested with aphids (Megoura viciae) and then sprayed with an EXAMPLE 25 Broad bean plants 3 5 cm. high were infested with aphids (Megaura viciae) and then sprayed with an aqueous dispersion containing 250 parts per million w/v of each of the carbamoyl imidazole compounds described in Examples 2 to 8 and 12 to 16. Each plant was kept under a lamp glass for 24 hours and then examined. It was found that all of the compounds gave at least a 50 percent control of the aahids. The aphid populations on control plants that had been treated with an aqueous spray not containing any test compound were not affected.
• EXAMPLE 26 An assessment of ovo-larvicidal activity against Te!- ranyclms urticae was made in the following way.
• the roots ofa rice seeding were dipped in an aqueous emulsion containing 0.005% by weight of the test compound.
• the rice seedling was enclosed in a glass cylinder into which fifteen adult green rice leafl1oppers were inserted and the temperature was maintained at 25C. After 48 hours the insect mortality was observed. It was found that a complete kill of the insects had occurred.
• R is selected from the group consisting of cyclopentyl and cyclohexyl optionally containing 1 to 3 methyl substituents.
• a method of combatting insects or acarids which comprises applying to said insects, acarids or the locus thereof an insectically or acaridically effective amount of a compound of the formula of (a) R and R are each selected from the group consisting of alkyl of l to 7 carbon atoms and alkenyl of 2 to 4 carbon atoms, and (b) R is alkyl of 1 'to 4 carbon atoms and R is selected from the group consisting of alkoxyalkyl of 3 to 6 carbon atoms and haloalkyl of l to 6 carbon atoms, together with a suitable carrier.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• General Health & Medical Sciences (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
• Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Dentistry (AREA)
• Agronomy & Crop Science (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Plural Heterocyclic Compounds (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)

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• 1972
  • 1972-07-26 GB GB3498172*[A patent/GB1408877A/en not_active Expired
  • 1972-11-30 US US311009A patent/US3868458A/en not_active Expired - Lifetime
  • 1972-12-05 AT AT1033572A patent/AT326948B/de not_active IP Right Cessation
  • 1972-12-07 NL NL7216602A patent/NL7216602A/xx not_active Application Discontinuation
  • 1972-12-07 DE DE2260025A patent/DE2260025A1/de active Pending
  • 1972-12-07 FR FR7243536A patent/FR2164350A5/fr not_active Expired
  • 1972-12-07 JP JP47123009A patent/JPS4862937A/ja active Pending
• 1973
  • 1973-05-25 BE BE131544A patent/BE800061A/xx unknown

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